A convenient method for N-1 arylation of uracil derivatives

Tetrahedron Letters

Volumn 47, Issue 27, 2006, Pages 4653-4657

  Gondela, Andrzej ^a   Walczak, Krzysztof ^a  

^a SILESIAN UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

1 (2,4 Dinitrophenyl) 5 nitrouracil; 5 Nitro 1 (4 nitrophenyl)uracil; 5 Substituted uracil derivatives; ANRORC type reaction; Nucleophilic aromatic substitution

Indexed keywords

1 (2,4 DINITROPHENYL)URACIL; 1 (4 NITROPHENYL)URACIL; 1 FLUORO 2,4 DINITROBENZENE; 1 FLUORO 4 NITROBENZENE; 5 CHLORO 1 (2,4 DINITROPHENYL)URACIL; BASE; UNCLASSIFIED DRUG; URACIL DERIVATIVE;

ARTICLE; ARYLATION; DRUG SYNTHESIS;

EID: 33744530854     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.130     Document Type: Article

References (22)

1. Block J.H., and Beale J.M. Organic Medicinal and Pharmaceutical Chemistry. 11th ed. (2004), Lippincott Williams & Wilkins, London 375-382 406-414
2. Longley D.B., Harkin D.P., and Johnston P.G. Nat. Rev. 3 (2003) 330-338
3. Hoffmann Ch., Rockstroh J.K., and Kamps B.S. HIV Medicine 2005 (2005), Flying Publisher; Steinhauser, Paris pp 620-683
4. Baraldi P.G., Romagnoli R., Guadix A.E., Pineda de las Infantas M.J.P., Gallo M.A., Espinosa A., Martinez A., Bingham J.P., and Hartley J.A. J. Med. Chem. 45 (2002) 3630-3638
5. Copik A., Suwiński J., Walczak K., Bronikowska J., Czuba Z., and Król W. Nucleosides, Nucleotides Nucleic Acids Res. 21 (2002) 377-383
6. Gondela A., and Walczak K. Tetrahedron Lett. 44 (2003) 7291-7293
7. Gondela A., Gabański R., and Walczak K. Tetrahedron Lett. 45 (2004) 8007-8009
8. Gondela A., and Walczak K. Tetrahedron: Asymmetry 16 (2005) 2107-2112
9. Winckelmann I., and Larsen E.H. Synthesis 12 (1986) 1041-1044
10. Gabel N.W., and Binkley S.B. J. Org. Chem. 23 (1958) 643-645
11. Singh H., Singh P., Aggarwal P., and Kumar S. J. Chem. Soc., Perkin Trans. 1 (1993) 731-735
12. Maruyama T., Fujiwara K., and Fukuhara M. J. Chem. Soc., Perkin Trans. 1 (1995) 733-734
13. Jacobsen S.A., Rødbotten S., and Benneche T. J. Chem. Soc., Perkin Trans. 1 (1999) 3265-3268
14. Meigh J.P., Álvarez M., and Joule J.A. J. Chem. Soc., Perkin Trans. 1 (2001) 2012-2021
15. Zhou T., Li T.-C., and Chen Z.-C. Helv. Chim. Acta 88 (2005) 290-296
16. Boga C., Bonmartini A.C., Fornali L., Modarelli V., Righi L., and Sgarabotto P. J. Chem. Res. (M) 12 (2001) 1217
17. Jang Y.H., Sowers L.C., Cagin T., and Goddard W.A. J. Phys. Chem. A 105 (2001) 274-280
18. 8 (323.18): C, 37.17; H, 1.56; N, 21.67. Found: C, 37.31; H, 1.72; N, 21.69.
19. 6 (278.18): C, 43.18; H, 2.17; N, 20.14. Found: C, 42.96; H, 2.21; N, 19.89.
20. Hirota K., Kitade Y., Sajki H., and Maki Y. J. Chem. Soc., Perkin Trans. 1 (1990) 367-373
21. 5 (201.14): C, 35.83; H, 3.51; N, 20.89. Found: C, 35.91; H, 3.62; N, 20.47.
22. 2), 8.11 (dd, 1H J = 2.7, 9.0 Hz, H-5), 9.00 (d, 1H, J = 2.7 Hz, H-3).